HCID 90333619, compound → HCID 178485243, compound

HRID 595695Notes

Reaction equation

HRID 595695 reaction equation
C([O:8][C:9]1[C:14]([N:15]([CH3:20])[S:16]([CH3:19])(=[O:18])=[O:17])=[CH:13][N:12]2[N:21]=[C:22]([C:28]3[CH:33]=[CH:32][C:31]([F:34])=[CH:30][CH:29]=3)[C:23]([C:24]([NH:26][CH3:27])=[O:25])=[C:11]2[CH:10]=1)C1C=CC=CC=1>C1COCC1.[Pd]>[F:34][C:31]1[CH:32]=[CH:33][C:28]([C:22]2[C:23]([C:24]([NH:26][CH3:27])=[O:25])=[C:11]3[CH:10]=[C:9]([OH:8])[C:14]([N:15]([CH3:20])[S:16]([CH3:19])(=[O:18])=[O:17])=[CH:13][N:12]3[N:21]=2)=[CH:29][CH:30]=1

Participants

4

Reactant 1

HCID 90333619HCID 90333619, compound

Product 1

HCID 178485243HCID 178485243, compoundYield 94.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A degassed solution of 5-(benzyloxy)-2-(4-fluorophenyl)-N-methyl-6-(N-methylmethylsulfonamido)pyrazolo[1,5-a]pyridine-3-carboxamide (3.0 g, 6.2 mmol) in THF (50 mL) was charged with 10% palladium on carbon (0.3 g). The reaction mixture was hydrogenated at room temperature under H2 balloon for 4 hours. The reaction mixture was filtered, and washed with DMF twice. The filtrate concentrated in vacuo and dried to afford pure 2-(4-fluorophenyl)-5-hydroxy-N-methyl-6-(N-methylmethylsulfonamido) pyrazolo[1,5-a]pyridine-3-carboxamide (2.3 g, yield: 94%). MS (M+H)+: 393.

Workup

  1. customwas hydrogenated at room temperature under H2
  2. customfor 4 hours
  3. filtrationThe reaction mixture was filtered
  4. washwashed with DMF twice
  5. concentrationThe filtrate concentrated in vacuo
  6. customdried

Sources & evidence

ORD record
ord-50d2b9741fb44e67a343b0d598f7647f
Source dataset
uspto-grants-2016_01
Patent number
US09243002B2

Reaction notes

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